Redting a shidduch with a previously married guy to a never married girl

This is a very dangerous situation.

A. You have to know why the guy is divorced. Maybe it was just a major-league mismatch, and maybe he was abusive. How will you find out? Divorces are like football matches in a way, everybody takes sides and defends their team/friend, so it’s difficult to find out what actually happened, doubly so if there was abuse. Why is this man looking for an unmarried girl? Perhaps because he thinks she’ll be naive enough not to know if he’s being abusive? The girl should be very, very careful.

B. Being married is a different planet. Until you actually get married you have no idea how closely you’ll be involved emotionally and practically with your spouse, and you have no idea what’s important and what isn’t. He’s asking for trouble, because he’ll risk getting misinterpreted all the time.

C. Why does this guy want a girl who’s never been married? Besides what I mentioned above, is it just a status thing for him? Has he got psychological issues?

This is not a place for people with realistic expectations to go, and if they do, they should do some serious couples counseling first.

Midwest2:

A. Your first concern is no different whether matching a divorced guy with a divorced girl or a divorced guy with a never married girl or a never married guy with a divorced girl.

Do you generically worry any divorced girl may have been abusive?

C. Who said he’s davka looking for an never bmarried girl? He may be open to a previously married girl or a never married one.

Additionally, according to Jewish tradition there’s a positive benefit to marrying a never married girl. So that is a good train he may be looking for such. Furthermore, it is a positive commandment to have children. That may be another reason.

The Chofetz Chaim and the Ribnitzer Rebbe, to take two recent examples that come to mind, married young never married women when they were in their old age. And the CC had more children.

Midwest, not necessarily. Consider these points:
First of all, slonimer asked when it is appropriate to redt such a shidduch- it does not mean that the man in question is only looking for a single girl.
However, here are some reasons why he may want a girl who has never been married:
1. he is a cohein
2. Blending families, dealing with 2 sets of exes and the accompanying baggage can lead to a lot of strain on a relationship. He may feel that his second marriage may have more chance of success if his wife was not previously married.
3. There are a lot of older, single girls out there, maybe more than divorcees/widows, so why should he limit himself?

From the never married girl’s point of view, if she is older and been dating for a long time, she may feel that a divorcee is more “normal” than a never been married guy in his 30s or 40s.

To address the OP, it really depends on the girl and how willing she is to think out of the box, and how hard it has been for her in the never been married shidduch scene. Age may open her to the suggestion, but I think the exact age will differ for each individual. The only way to know is to ask what she wants, what she is willing to try- and to do it in a respectful, understanding way and not a pushy manner. She also may be more open to the idea for a specific suggestion that is very appropriate, rather than as a general, theoretical idea.

And yes, of course she needs to be careful and try to get objective info about him, and make sure he is not abusive or have psychological issues that can impede a marriage (and by the way, not-having-been-married-yet doesn’t guarantee that a guy doesn’t have those issues..). It will be helpful to her if you can provide as many answers and as much background as you can.

Phil, thank you for the correction about the CC’s second rebbetzin. She was married previously but she was young when marrying the much older Chofetz Chaim. In fact she survived WWII and lived in America after the war and her kever is in Queens.

Regarding the Ribnitzer Rebbe, I believe his second rebbetzin, who was far younger than him, was never married before marrying the Ribnitzer nor after he was niftar.